Studies on the Relationship between the Structures of Tartaric Acid Derivatives and Their Optical Activities

Abstract

Abstract: Several L-tartaric acid derivatives (1～6) were synthesized and their specific rotations were measured. It was found that diester 3 exhibited an unusually high negative value of specific rotation([α]_D²⁵-45.03 °，DMSO]), its amide derivative s 4 showed slightly positive specific rotation (4a:+11.19°,4b:+2.14°)，and the reduction products showed slightly negative values (5a:-0.52°, 5b:-4.92°，6：-2.95°). The optical activities o f 1～6 were elucidated by the polarization ability of functional gro ups and the helical structures.

Key words: tartaric acid derivatives, helical structure, specific rotation, optical activity

摘要： 合成出系列的L-半螺旋型酒石酸衍生物1～6，测定比旋光度，发现酒石酸二乙酯2([α]_D²⁵+3.00°，DMSO)形成2，3-O-亚异丙基酒石酸二乙酯3后旋光急剧往左偏移([α]_D²⁵-45.03 °，DMSO])，3酰胺化后比旋光值往右偏移(4a ：+11.19°，4b：+2.14°)，还原产物的比旋光值往左偏移(5a：-0.52°， 5b ：-4.92°，6：-2.95°)；并用分子的螺旋结构与基团的极化性质研究旋光规律。

关键词: 酒石酸衍生物, 螺旋结构, 比旋光度, 光学活性

CLC Number:

LIN Chongxi,LIU Jingyuan,WANG An,YE Xiulin. Studies on the Relationship between the Structures of Tartaric Acid Derivatives and Their Optical Activities[J]. Acta Scientiarum Naturalium Universitatis Pekinensis.

林崇熙,柳敬元,王安,叶秀林. 酒石酸衍生物的合成及其结构与光学活性关系的探讨[J]. 北京大学学报（自然科学版）.

[1]	XU Xuefeng,YAN Sha,WANG Keming,WANG Xuelin,XUE Jianming,WANG Yugang. Gas-Assisted Etching of Micro-Hole Lattice Array on Lithium Niobate with Focused Ion Beam [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2009, 45(6): 937-940.
[2]	WANG Hui,PEI Weiwei,ZHANG Shiwei,SUN Guobin. Synthesis and Crystal Structure of(R)-2-Hydroxymethyl-1-aza-4-thiaspiro［4.5］decane [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2004, 40(6): 849-854.
[3]	SHEN Hongyan,ZHOU Chuang,YE Yunhua,TIAN Guiling. Stability of α-Chymotrypsin in Different Media [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2004, 40(4): 578-582.
[4]	CHEN Jiahua,ZHANG Yandong. Total Synthesis of Acyl- and Alkyl- LPA [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2003, 39(2): 151-157.
[5]	MENG Yuanru,GUAN Yedi. A New Method for α-Alkylation of γ-Butyrolactone [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2003, 39(2): 277-280.
[6]	GUO Yong'en,WANG Nengdong,CHEN Jiahua,ZOU Feng,CHEN Liumin,JIN Sheng,FU Bin,ZHANG Xiu,ZHANG Yandong,YOU Zejin,LIU Dongmei. Synthesis of Chiral Glycerol Derivatives [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2002, 38(6): 744-749.
[7]	SUN Guobin,PEI Weiwei,WU Yongqing,HUO Jun,YE Weiping. Enantioselective Borane Reduction of Prochiral Ketones Catalyzed by (S)-(indolin-2-yl) methanol or (S)-indoline-2-carboxylic Acid [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2002, 38(6): 846-849.
[8]	YANG Ao,ZHANG Yawei,LI Kunyu,GUAN Yedi. The Synthesis and Resolution of the Optical Active Derivatives of Ketorolac [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2002, 38(2): 169-174.
[9]	ZHAO Xianrui,LI Chongxi. Synthesis of Some Esters of Acids Containing Nitrogen with Metronidazole [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2002, 38(2): 175-180.
[10]	CHEN Xiong,LI Chongxi,MA Weiyong. Synthesis of Coumarin Derivatives Using Microwave Irradiation [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2002, 38(2): 268-270.
[11]	CHEN Yantao,HUA Wenting. Formation of the p-Toluenesulphinyl Anion from the Diester of N-Tosyl Alanine with 2, 6-Bis(hydroxylmethyl) pyridine and Its Nucleophilic Addition Product with 2, 6-Bis(chloromethyl) pyridine [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2001, 37(4): 439-443.
[12]	JIANG Nan,WANG Lin,WANG Jianbo. The Reaction Mechanism and Synthetic Application of α-Diazo Carbonyl Compounds [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2001, 37(4): 570-576.
[13]	JIANG Nan,WANG Lin,WANG Jianbo. The Reaction Mechanism and Synthetic Application of α-Diazo Carbonyl Compounds [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2001, 37(4): 570-576.
[14]	HOU Shifeng,LI Qiguang,LIU Zhongfan. The Morphology of Self-assembled Monolayers of Mercapto Methoxy Poly(ethylene glycol) and Its Complex with Poly(acrylic acid) [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2001, 37(2): 145-148.
[15]	GAO Wentao,ZHENG Zhuo,CHEN Huilin. Study on Synthesis and Reactions of Acetyl-substituted Troponoids With Aromatic Aldehyde [J]. Acta Scientiarum Naturalium Universitatis Pekinensis, 2001, 37(2): 205-209.

Studies on the Relationship between the Structures of Tartaric Acid Derivatives and Their Optical Activities

酒石酸衍生物的合成及其结构与光学活性关系的探讨

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics